AI is reshaping industries, from cybersecurity enterprise platforms to news sites that rate stories for bias, balance, and representation of opposing perspectives. But applying AI to legal workflows presents unique challenges.
As AI becomes more embedded in daily workflows, we set out to design a contract automation tool for law firms and independent lawyers—one that wouldn’t just automate tasks but enhance their decision-making.
The goal was to reduce contract negotiation time as much as possible—ideally by 90%—by focusing on three key areas:
- Automating redlines and comments to speed up contract review.
- Building expert Playbooks tailored to standards like oneNDA and oneDPA.
- Providing an AI assistant for real-time risk evaluation, clause drafting, and negotiation support.
But how do you design AI for a profession built on precedent, risk assessment, and trust—especially when some lawyers have never used AI and others are skeptical of it?
As any other meticulously designed product, we began by benchmarking competitors to gather insights and inspiration. We then created wireframes and showcased some of the user journeys with high-profile lawyers to collect feedback and iterate the product over various months.
Another major challenge was ensuring the AI understood contracts in a lawyer-friendly way. By leveraging large language models (LLMs), the platform could analyze agreements directly within Microsoft Word and apply Playbook rules accordingly.
For example, the AI can,
- Identify choice of law clauses that conflict with yours,
- Flag potential risks such as liabilities that exceed your usual agreements,
- Generate missing clauses, specific to your instructions or considerations.

Modern users expect AI to function like a GPT (Generative Pre-trained Transformer). This means they want to be able to ask questions in natural language and receive assistance that helps them complete tasks more efficiently. To address this need, we identified the most common questions a lawyer reviewing an agreement might ask themselves or a colleague and have prepared the appropriate tools – or “quick actions” to support these tasks.

Technology is at its best when it simply disappears from the awareness of the users and blends with the rest of their lifestyle and SimpleAI is well on its way to become the easiest – or rather, simplest – and more efficient platform of its kind to make the contract review and drafting experience more insightful and faster than ever.
Wrapping up, we learnt how to understand technology and the ways we can incorporate it into useful, meaningful experiences and platforms that impact real businesses, real people and make everyday tasks easier; how each industry can take advantage of AI and finally, how to work very closely with stakeholders and industry experts to consolidate the best ideas into a solid, real product.